In honor of Taylor Swift’s latest album, Life of a Showgirl, we’re celebrating by imagining a day in Woodstock, IL through the lens of her iconic albums. Each era tells a story, and so does our town — from morning strolls at the Farmers Market to a dazzling finale at the historic Opera House, there’s a little something for every Swiftie.
Here’s your guide to living the Life of a Woodstock Girl, Taylor’s Version:
1. Taylor Swift (2006) — Woodstock Farmers Market
Start your day like Taylor’s debut era…fresh, hopeful, and full of small-town charm. Stroll past colorful produce, grab a pastry, and soak in the warmth and energy of a true hometown morning, just like the spirit of Taylor Swift.
2. Fearless (2008) — The Paradox Squared Escape Room
Channel your brave side with friends and tackle puzzles together. Just like Fearless, this stop is all about taking risks, working as a team, and celebrating victory when you escape!
3. Speak Now (2010) — Classic Cinemas Woodstock Movie Theatre
Step into a story. Popcorn, comfy seats, and dramatic twists mirror the storytelling and confessions of Speak Now.
4. Red (2012) — Tommy’s Red Hots
What could be more classic with Red than… Red Hots? Grab a Chicago-style dog, savor the flavor, and enjoy a fun twist on Taylor’s iconic album.
5. 1989 (2014) — Fulfilled Thrift
Style, reinvention, and fearless energy — that’s 1989. Hunt for vintage gems or bold statement pieces that channel Taylor’s iconic confidence, and don’t forget to snap a photo of your favorite find.
6. Reputation (2017) — The Records Department
Dark, edgy, and unapologetic…that’s Reputation. Explore this cozy indie record store, flip through vinyl treasures, and pick up one of Taylor’s records to take home. From rare finds to timeless classics, this stop captures the bold, independent spirit of the album.
7. Lover (2019) — Winestock Wine Market
Raise a glass to friendship (or romance!) at Winestock Wine Market. Share a flight or a full glass, explore wines from near and far, and enjoy a cozy, eclectic spot that feels as whimsical and colorful as Taylor’s Lover era.
8. Folklore (2020) — Emricson Park Woods Walk Trail
Step into the quiet magic of Folklore along the Emricson Park trail. With a shaded path and dappled light through the trees, it’s the perfect spot to take a selfie or photo and reimagine the album cover. Pause, reflect, and connect with nature like Taylor’s wistful, storytelling era.
9. Evermore (2020) — Ryder’s Woods
Discover hidden paths and quiet corners in Ryder’s Woods. Evermore is full of mystery and gentle intrigue, and this woodland escape is your chance to experience that same sense of wonder right in Woodstock.
10. Midnights (2022) — Emerson & Oliver
Step into the secret, sultry world of Midnights at this password-protected speakeasy. Sip delicious, cleverly-crafted cocktails, enjoy live music, and soak in the intimate, late-night energy — perfect for channeling Taylor’s contemplative, after-dark era.
11. Tortured Poets Department — Atrocious Poets (inside the Woodstock Mall)
Dive into the theatrical world of Atrocious Poets, where interactive poetry, dramatic flair, and creative expression collide. Play with words, explore quirky exhibits, and let your inner poet take the spotlight. This fun, unpredictable stop celebrates creativity in true Swiftie style.
12. Life of a Showgirl (2025) — Woodstock Opera House
Step into the spotlight at the historic Woodstock Opera House and bring Life of a Showgirl to life. From the grand stage to the elegant auditorium, this is your chance to channel your inner performer, twirl, pose, and celebrate the drama, glamour, and excitement of Taylor’s newest album.
✨Think you have what it takes to complete the Swiftie Challenge? Let us know! Share your favorite moments on social media and tag @RealWoodstock to show how you’re living the Life of a Woodstock Girl, Taylor’s Version.